Dimethyl Sulfate → 1-Bromo-4-(2-methoxyethoxy)benzene

To an ice-cooled solution of 4-bromophenoxyethanol (5 g, 23.0 mmol) in THF (30 ml) was added a suspension of sodium hydride (1.10 g, 46.1 mmol) in THF (30 ml), with stirring. After 20 minutes dimethyl sulfate (4.37 ml, 46.1 mmol) was added dropwise. The reaction mixture was stirred for 4 hours at room temperature then quenched slowly with saturated aq. ammonium chloride (50 ml). The mixture was extracted with ethyl acetate (100 ml) and the organic extract was washed successively with 1M hydrochloric acid (50 ml) and brine (50 ml), dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure to leave 4-(2-methoxy-ethoxy)-bromobenzene (5.5 g, ca. quant.) as a pale brown oil. 1H-NMR; δ (CDCl3), 7.36 (2H, d, J=9.1 Hz), 6.80 (2H, d, J=9.1 Hz), 4.09 (2H, t, J=4.7 Hz), 3.74 (2H, t, J=4.7 Hz) and 3.45 (3H, s).

1. additionwas added
2. stirringThe reaction mixture was stirred for 4 hours at room temperature
3. customthen quenched slowly with saturated aq. ammonium chloride (50 ml)
4. extractionThe mixture was extracted with ethyl acetate (100 ml)
5. extractionthe organic extract
6. washwas washed successively with 1M hydrochloric acid (50 ml) and brine (50 ml)
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. customThe solvent was removed under reduced pressure

ORD record

ord-3f307cc1371c4e5ba81e84068026e4a5

Source dataset

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05840974